2-(Chloromethyl)-3,5-dimethyl-4-methoxypyridine hydrochloride → (4-Methoxy-3,5-dimethylpyridin-2-yl)methanamine

HRID 1246741Notes

Reaction equation

HRID 1246741 reaction equation
Cl.Cl[CH2:3][C:4]1[C:9]([CH3:10])=[C:8]([O:11][CH3:12])[C:7]([CH3:13])=[CH:6][N:5]=1.[NH3:14].CO>>[NH2:14][CH2:3][C:4]1[C:9]([CH3:10])=[C:8]([O:11][CH3:12])[C:7]([CH3:13])=[CH:6][N:5]=1

Participants

3

Reactant 2

HCID 116942582-(Chloromethyl)-3,5-dimethyl-4-methoxypyridine hydrochlorideHCID 21705897Ammonia methanol

Product 1

HCID 14645997(4-Methoxy-3,5-dimethylpyridin-2-yl)methanamineYield 76%

Procedure

A solution of 2-chloromethyl-4-methoxy-3,5-dimethyl-pyridine HCl (Aldrich 3.7 g, 16.6 mmole) in 7N NH3/MeOH (Aldrich, 200 mLs) was refluxed in a steel bomb for 15 hours. Removed the solvent under reduced pressure, the residue was taken into 5% MeOH/CH2Cl2 and filtering it through a thin layer of silica gel afforded the product at 76% yield. HPLC RT was 2.850 min. 1HNMR (CDCl3) δ 8.18 (s, 1H), 4.32 (s, 2H), 3.76 (s, 3H), 2.23 (s, 3H), 2.18 (s, 3H).

Workup

  1. customRemoved the solvent under reduced pressure
  2. filtrationfiltering it through a thin layer of silica gel
  3. customafforded the product at 76% yield

Sources & evidence

ORD record
ord-ece0513aef804fed93a1e7264051c05f
Source dataset
uspto-grants-2006_10
Patent number
US07129244B2

Reaction notes

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